US4229354A - Method of preparing alkali metal complex compounds - Google Patents

Method of preparing alkali metal complex compounds Download PDF

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US4229354A
US4229354A US05/905,489 US90548978A US4229354A US 4229354 A US4229354 A US 4229354A US 90548978 A US90548978 A US 90548978A US 4229354 A US4229354 A US 4229354A
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lithium
reaction
alkali metal
sodium
compound
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Borislav Bogdanovic
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Studiengesellschaft Kohle gGmbH
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2291—Olefins
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B21/00—Nitrogen; Compounds thereof
    • C01B21/06—Binary compounds of nitrogen with metals, with silicon, or with boron, or with carbon, i.e. nitrides; Compounds of nitrogen with more than one metal, silicon or boron
    • C01B21/0607—Binary compounds of nitrogen with metals, with silicon, or with boron, or with carbon, i.e. nitrides; Compounds of nitrogen with more than one metal, silicon or boron with alkali metals
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B21/00—Nitrogen; Compounds thereof
    • C01B21/06—Binary compounds of nitrogen with metals, with silicon, or with boron, or with carbon, i.e. nitrides; Compounds of nitrogen with more than one metal, silicon or boron
    • C01B21/0607—Binary compounds of nitrogen with metals, with silicon, or with boron, or with carbon, i.e. nitrides; Compounds of nitrogen with more than one metal, silicon or boron with alkali metals
    • C01B21/061—Binary compounds of nitrogen with metals, with silicon, or with boron, or with carbon, i.e. nitrides; Compounds of nitrogen with more than one metal, silicon or boron with alkali metals with lithium
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B6/00—Hydrides of metals including fully or partially hydrided metals, alloys or intermetallic compounds ; Compounds containing at least one metal-hydrogen bond, e.g. (GeH3)2S, SiH GeH; Monoborane or diborane; Addition complexes thereof
    • C01B6/04—Hydrides of alkali metals, alkaline earth metals, beryllium or magnesium; Addition complexes thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/02—Five-membered rings
    • C07D339/04—Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/62—Reductions in general of inorganic substrates, e.g. formal hydrogenation, e.g. of N2
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
    • B01J2531/11—Lithium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
    • B01J2531/12—Sodium

Definitions

  • the present invention relates to a method of preparing alkali metal hydrides and nitrides by means of easily accessible, new alkali metal complex compounds as well as said new alkali metal complex compounds and their preparation.
  • Alkali metal hydrides such as for example lithium hydride or sodium hydride, are formed, as it is known, from the elements lithium and hydrogen at temperatures above 300° C., and especially at temperatures around 700° C. (Kirk-Othmer 1967, Vol. 12, p. 544; Ullmann, Vol. 8, 1957, p. 723). At room temperature, hydrogen does not react with lithium, and is not absorbed by metal no matter how finely divided (E. Wiberg and E. Amberger, "Hydrides of the Elements of Main Groups I-IV,” Elsevier Publishing Co., 1971, p. 19).
  • the temperature for the preparation of lithium hydride can be reduced to 310° to 345° C., and in the presence of lithium stearate as catalyst, it can be reduced to from 240° to 330° C.
  • catalysts of sodium stearate are used for the preparation of sodium hydride. At a temperature of less than 200° C., it has not been possible to prepare lithium hydride to date. The lowest temperature yet given for the preparation of potassium hydride is 140° C. (Methodicum Chim., Vol. 7, pp. 10-12).
  • the alkali metal complex compounds used as catalysts contain several metal atoms per molecule, and can be represented by the General Formulas I and II: ##STR1## wherein Me represents an alkali metal, X sulfur or oxygen, n a whole number from 3 to 20, L and L' are each mono or polyfunctional ethers or amines, p and q are whole numbers from 0 to 4, R 1 , R 2 , R 3 and R 4 hydrogen, alkyl, cycloalkyl, aralkyl or aryl moieties, and/or two or more such moieties closed to form an aliphatic or aromatic mono- or polycyclic ring system (preferably not all of the R 1 , R 2 , R 3 and R 4 are hydrogen).
  • alkyl preferably contains 1 to 12 (particularly 1 to 6) carbon atoms; cycloalkyl preferably contains 3 to 8, (particularly 5 to 6) ring members; aralkyl preferably contains 1 to 12 (particularly 1 to 6 and more particularly 1 to 2) carbon atoms in the alkyl portion and is preferably mono- or bi-cyclic carbocyclic in the aryl portion to include in the aryl portion e.g. phenyl, naphthyl and biphenyl; aryl is defined as shown above for the aryl portion of aralkyl moieties.
  • rings are preferably between R 1 and R 2 or R 2 and R 3 and R 4 and are preferably aromatic rings.
  • Preferred polycyclic ringsystems contain rings between R 1 and R 2 , as well as additionally between R 3 and R 4 .
  • the number of alkali metal atoms in the alkali metal complexes which can be prepared by the present method depends to some extent on the structure of the compound III to VII that is used in each case or on the nature of their substituents, on the alkali metal, on the ether or amine that is used, and on the conditions of the reaction.
  • lithium in THF at 0° C 1,2,-dithiol-3-thione
  • alkali metal atoms in alkali metal complexes I and II is generally very much greater than two when compounds III to VIII with phenyl groups as substituents are used.
  • the alkali metal complexes which can be made by the present method having more than two alkali metal atoms, are highly reactive organometallic compounds which are sensitive to air and moisture, so that their preparation must be performed in an inert gas atmosphere.
  • the alkali metal complexes which can be prepared by this method can be obtained in solution and put to use in dissolved form, and they can also be used in solid, finely divied form in the catalysis.
  • the claimed alkali metal complexes containing several alkali metal atoms per molecule can be used either as such or in combination with transition metal compounds, for example, for the preparation of alkali metal hydrides, the fixing of molecular nitrogen, and as hydrogenation catalysts.
  • the complex isolated in solid form is soluble in THF and can be re-precipitated with the same composition by the addition of pentane to the THF solution.
  • the solution was concentrated in vacuo (0.2-0.3 Torr) to 25 ml, and 20 ml of 1,2-dimethoxyethane was added, whereupon a black precipitate formed.
  • the suspension was let stand for 3 h at 0° C., the precipitate was filtered from the dark-colored solution, and the precipitate was vacuum dried (20° C., 10 -4 Torr) to constant weight. 0.82 g (51.5%) was obtained of the highly air-sensitive complex compound:
  • the decalithium complex was obtained in the form of its 1:1 adduct with THF: ##STR8## in a yield of 2.84 g (90.8% of the theory) in solid form.
  • the hydrolysis and deuterolysis (Equation 1) of this complex compound can serve for its chemical characterization.
  • the hydrolysis of the complex in solid form (as the THF adduct) or in THF solution yields lithium hydroxide, lithium sulfide (80% yield with respect to the sulfur bound in the complex) plus a mixture of C 17 hydrocarbons consisting of isomers of 1,5-diphenyl-1,3-pentadiene and a small amount of 1,5-di-phenylpentenes (total yield of C 17 hydrocarbons, approximately 70% of the theory).
  • the hydrolysis reaction and deuterolysis reaction can be considered as proof of the constitution of the hydrocarbon structure that is the basis of the complex.
  • the excess lithium was filtered from the solution, 33 ml of tetramethylenediamine is added, and the mixture is concentrated in vacuo to 40 ml.
  • 0.38 g (66% of the theory) of the heptalithium complex compound of (7) is obtained in the form of its 1:1 adduct with tetramethylethylenediamine and THF:
  • Example 10 In a manner similar to Example 1, 0.57 g (2.73 mMol) of 4-phenyl-1,2-dithiol-3-thione (8) was reacted with 2.34 g (102 mAtom) of sodium sand in 100 ml of THF at 0° C. As in Example 10, the course of the reaction was pursued by taking samples (15.0 ml) and by acidimetric determination of the sodium in the samples. The course of the reaction is indicated by the following table:
  • a heptasodium complex of compound (8) forms from the latter and sodium in THF at 0° C.
  • the amount of hydrogen gas absorbed (1740 ml of H 2 of 20° C./760 Torr) corresponded to a transformation of 101% of the input lithium to lithium hydride, and signifies that 60 moles of lithium hydride had formed per mole of the catalyst.

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  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
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US05/905,489 1977-05-17 1978-05-12 Method of preparing alkali metal complex compounds Expired - Lifetime US4229354A (en)

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DE19772722221 DE2722221A1 (de) 1977-05-17 1977-05-17 Alkalimetallkomplexverbindungen, verfahren zu ihrer herstellung und ihre verwendung zur hydrierung und nitridierung von alkalimetallen
DE2722221 1977-05-17

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US06/274,947 Expired - Fee Related US4370488A (en) 1977-05-17 1981-06-18 Alkali metal complex compounds
US06/426,495 Expired - Fee Related US4396589A (en) 1977-05-17 1982-09-29 Alkali metal complex compounds, and their use in the hydrogenation and nitridation of alkali metals

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US06/426,495 Expired - Fee Related US4396589A (en) 1977-05-17 1982-09-29 Alkali metal complex compounds, and their use in the hydrogenation and nitridation of alkali metals

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JP (5) JPS53144532A (ru)
AT (1) AT365604B (ru)
BE (1) BE867155A (ru)
CA (1) CA1117738A (ru)
CH (1) CH635825A5 (ru)
DE (1) DE2722221A1 (ru)
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ES (1) ES469874A1 (ru)
FR (1) FR2391196A1 (ru)
GB (1) GB1598230A (ru)
IE (1) IE46897B1 (ru)
IT (1) IT1096296B (ru)
LU (1) LU79670A1 (ru)
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4365088A (en) * 1980-07-03 1982-12-21 Solvay & Cie Process for the manufacture of β-hydroxybutyric acid and its oligocondensates
US4396589A (en) * 1977-05-17 1983-08-02 Studiengesellschaft Kohle Mbh Alkali metal complex compounds, and their use in the hydrogenation and nitridation of alkali metals
US5206394A (en) * 1987-10-21 1993-04-27 The Associated Octel Company Limited Lewis base complexes of alkali metal salts
WO2014170429A1 (de) * 2013-04-19 2014-10-23 Rockwood Lithium GmbH Stabilisierte mit einer stickstoffhaltigen schale beschichtete lithiummetallabformungen und verfahren zu deren herstellung

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DE2908928A1 (de) * 1979-03-07 1980-09-18 Studiengesellschaft Kohle Mbh Verfahren zur herstellung von organolithiumverbindungen neben lithiumhydrid
JPS63161142U (ru) * 1987-04-09 1988-10-21
JPH04122505U (ja) * 1991-04-23 1992-11-04 株式会社富士製作所 ごみ容器
US5506863A (en) * 1993-08-25 1996-04-09 Motorola, Inc. Method and apparatus for operating with a hopping control channel in a communication system
TW583027B (en) * 1998-10-30 2004-04-11 Shell Int Research A method for preparing a hydrogenation catalyst system
ATE275568T1 (de) * 1999-01-19 2004-09-15 Basf Ag Herstellung von alkalimetall-substituierten borohydridreagenzien
WO2005080266A1 (en) * 2004-02-13 2005-09-01 The Research Foundation Of State University Of New York Method for producing a reversible hydrogen storage medium with high storage capacity and ultrafast kinetics
US7537747B2 (en) * 2004-06-03 2009-05-26 Gm Global Technology Operations, Inc. Hydrogen storage mixed gas system method
WO2006073004A1 (ja) * 2005-01-06 2006-07-13 Shieldtechs, Inc. 防錆性および導電性に優れた樹脂組成物並びに樹脂組成物被覆部材
US20070148076A1 (en) * 2005-02-14 2007-06-28 Yun Hang Hu Method for producing a reversible hydrogen storage medium with high storage capacity and ultrafast kinetics
WO2007002039A2 (en) * 2005-06-20 2007-01-04 University Of South Carolina Physiochemical pathway to reversible hydrogen storage
US8153554B2 (en) 2006-11-15 2012-04-10 University Of South Carolina Reversible hydrogen storage materials
EP3277624B1 (de) 2015-04-02 2020-05-06 Albemarle Germany GmbH Hochreaktive metallhydride, verfahren zu deren herstellung und anwendung
JP7088912B2 (ja) 2016-09-15 2022-06-21 シティ・オブ・ホープ ジチオｅｔｐ誘導体
US11230560B2 (en) 2017-05-22 2022-01-25 City Of Hope Synthesis of ETP derivatives
CN111132985B (zh) * 2017-09-20 2024-01-02 莫门蒂夫性能材料股份有限公司 用于制造甲基氯氢单硅烷的集成工艺

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US3153087A (en) * 1960-12-30 1964-10-13 Pure Oil Co Process for producing alkali metal adducts of aromatic solvent extracts of petroleum fractions, the products thereof and carbonation of the products
US3351631A (en) * 1963-12-02 1967-11-07 Union Oil Co Recovery and fractionation of complex acids

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US3617218A (en) * 1968-11-13 1971-11-02 Us Health Education & Welfare Catalytic synthesis of metallic hydrides
DE2402399C3 (de) * 1974-01-18 1979-11-08 Wacker-Chemie Gmbh, 8000 Muenchen Verfahren zur Herstellung von Alkaliacetylacetonaten
DE2722221A1 (de) * 1977-05-17 1978-11-23 Studiengesellschaft Kohle Mbh Alkalimetallkomplexverbindungen, verfahren zu ihrer herstellung und ihre verwendung zur hydrierung und nitridierung von alkalimetallen
DE2908928A1 (de) * 1979-03-07 1980-09-18 Studiengesellschaft Kohle Mbh Verfahren zur herstellung von organolithiumverbindungen neben lithiumhydrid

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3153087A (en) * 1960-12-30 1964-10-13 Pure Oil Co Process for producing alkali metal adducts of aromatic solvent extracts of petroleum fractions, the products thereof and carbonation of the products
US3351631A (en) * 1963-12-02 1967-11-07 Union Oil Co Recovery and fractionation of complex acids

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4396589A (en) * 1977-05-17 1983-08-02 Studiengesellschaft Kohle Mbh Alkali metal complex compounds, and their use in the hydrogenation and nitridation of alkali metals
US4365088A (en) * 1980-07-03 1982-12-21 Solvay & Cie Process for the manufacture of β-hydroxybutyric acid and its oligocondensates
US5206394A (en) * 1987-10-21 1993-04-27 The Associated Octel Company Limited Lewis base complexes of alkali metal salts
WO2014170429A1 (de) * 2013-04-19 2014-10-23 Rockwood Lithium GmbH Stabilisierte mit einer stickstoffhaltigen schale beschichtete lithiummetallabformungen und verfahren zu deren herstellung
KR20160004312A (ko) * 2013-04-19 2016-01-12 록우드 리튬 게엠베하 질소 함유 쉘로 코팅된 안정화된 리튬 금속 형성물 및 이를 생산하는 방법
CN105392737A (zh) * 2013-04-19 2016-03-09 罗克伍德锂有限责任公司 用含氮壳涂敷的稳定化的锂金属结构及其制造方法
US10160036B2 (en) 2013-04-19 2018-12-25 Albemarle Germany Gmbh Stabilized lithium metal formations coasted with a shell containing nitrogen, and a method for the production of same
KR102258042B1 (ko) 2013-04-19 2021-05-27 알베마를 저머니 게엠베하 질소 함유 쉘로 코팅된 안정화된 리튬 금속 형성물 및 이를 생산하는 방법

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GB1598230A (en) 1981-09-16
IT7823502A0 (it) 1978-05-17
SU1003758A3 (ru) 1983-03-07
ES469874A1 (es) 1979-01-01
JPS62187474A (ja) 1987-08-15
DE2722221C2 (ru) 1987-09-24
AT365604B (de) 1982-02-10
IE780986L (en) 1978-11-17
JPS63265803A (ja) 1988-11-02
IT1096296B (it) 1985-08-26
JPS6225650B2 (ru) 1987-06-04
IE46897B1 (en) 1983-10-19
FR2391196B1 (ru) 1983-11-25
BE867155A (fr) 1978-09-18
DE2722221A1 (de) 1978-11-23
JPH0233643B2 (ru) 1990-07-30
CH635825A5 (de) 1983-04-29
JPS62182103A (ja) 1987-08-10
LU79670A1 (de) 1978-11-06
NL7805356A (nl) 1978-11-21
DK217078A (da) 1978-11-18
FR2391196A1 (fr) 1978-12-15
JPH0130835B2 (ru) 1989-06-22
JPS62174088A (ja) 1987-07-30
JPS53144532A (en) 1978-12-15
CA1117738A (en) 1982-02-09
JPS6346078B2 (ru) 1988-09-13
US4370488A (en) 1983-01-25
ATA352878A (de) 1981-06-15
US4301081A (en) 1981-11-17
US4396589A (en) 1983-08-02
MX149368A (es) 1983-10-28

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